I like Sale's deal, but there's risk involved for both the Sox and the player, and such high numbers in later years could be a millstone if he gets hurt and can't live up to potential. I'd have preferred a shorter deal, then an un-Jerry like move of paying the guy what he's worth if he becomes what we think he can.

High number? Are you posting from 1980? There's only one guaranteed year worth over $10 M, which is EXTREMELY reasonable in this day in age for a pitcher of his quality. I don't see the shorter term deal logic, either, Sale was already under the Sox's control for 4 years, so all they've essentially done is extend is contract 1 extra guaranteed year but eliminated the uncertainty of price for the length of his deal. Pretty much any smart team or GM; Tampa Bay, San Francisco, St. Louis, etc. is making these moves nowadays.